I’ve been helping other people get started with their own experiments in delegation, and one of them asked me how I manage my team in oDesk. Here’s how I do it.

Setting expectations

I like thinking of oDesk contracts as mini-experiments. It’s not about hiring amazing people – as in the regular job market, amazing people usually have their plates full of work and don’t have to look for more (aside from word of mouth). Each hire is an experiment involving the process and the person. If it works out, wonderful; I’ll keep them on as long as I can find work for them to do. If it doesn’t – and there have been some gigs that were just not a good fit – well, it’s only a small experiment.

I like taking notes so that I can hire people again for other things. Many people move on from oDesk after some time, though, so I haven’t always been able to go back and rehire people who have worked out. I try to focus on developing good processes instead of relying only on hiring good people, though, so I don’t mind turnover so much. I sometimes have to refer to my notes to remember whom to send tasks to, though!

Someday I might graduate to having one or two assistants with more time dedicated to my tasks. In the meantime, this patchwork of assistants requires a little bit more oversight.

Posting a job ad

I usually post my job ads for as-needed work, 1-3 months, < 10 hours a week. This gives me the flexibility to experiment on a low-commitment basis.

In addition to describing my requirements, I also ask that job applications show their attention to detail by beginning and ending their cover letter with an unusual keyword, such as “blue”. This makes it super-easy to filter out people who are indiscriminately applying to job posts or who don’t read the requirements all the way through. Many people put in the first keyword, and a few remember to put in the last keyword as well.

I often ask people to include a sample of their relevant work in their cover letter, and to describe their experience (especially for skills that are optional but useful). I detest the scammy practice of asking people to do unpaid work as part of their application, so I only ask for existing work samples.

Stephan Spencer (one of my delegation role models) uses a riddle in his job application / interview process as a way of testing people’s thinking. He spins one of the classic riddles into something that’s not easily Googleable, so he can see if people can figure things out on their own.

As mentioned, I use attention to detail as one of my quick filters for applications.

I usually also search and filter by 4.0+ rating, > 100 hours on oDesk, but I’ll look at the reviews even for people with lower rating if I like their profile. I’ll occasionally take a chance on people who are new to oDesk – everyone’s got to start somewhere – with the expectation that I’ll need to teach them a little more about working with me or using oDesk to file time.

It’s always a treat to find good people in the Philippines because I’m from there as well, so the shared cultural background makes interviewing and working a little bit easier.

Inviting specific people

When I come across interesting people’s profiles, I save their profile in oDesk or Evernote (Evernote is easier to browse/search). After I post the job, I invite them to participate. There are so many good people looking for work, though, so I don’t often do this.

I occasionally create private job posts and invite specific people to them. I more often post public job posts even though I invite specific people to them, because you never know what kind of awesome talent is out there.

Interviewing applicants

I want to confirm that people understand the job requirements, find out how much they meet the requirements, and – also important – learn more about their other skills and their career goals so that I can come up with more tasks that fit them.

I use ScheduleOnce to schedule Skype interviews. The timezone difference and the interface turn out to be useful filters for attention to detail and willingness to deal with unknown tools. For virtual assistant positions, communication skills and trust are key, so I like talking to people first.

I also want to answer any questions they have. Contractors take on some risk whenever they accept a contract, as there have been quite a few employers who have scammed them into unpaid work or feedback blackmail. I want to give them the opportunity to make sure I’m not crazy, too. =)

I’m working on improving my interview process. In particular, I’m going to start asking people to tell me a story about the time they were wrong about something or the time that they argued with someone. Talking to my mom about her HR issues (and now, sorting through my own!), I’m beginning to realize the importance of understanding people’s conflict/disagreement resolution strategy and whether they can maintain calm and respect under stress.

For straightforward tasks like transcription, I might hire someone without ever talking to them in real-time, because I can “interview” them in the process of them working on their first paid task.

Hiring and onboarding

After we answer each other’s questions satisfactorily, I go ahead and set up the contract. For virtual assistants who will be communicating with other people on my behalf, I’ll set up a Google Apps account. LastPass makes it easy to share and revoke passwords, and I’ve also started the habit of keeping track of who has access to which accounts in order to simplify offboarding them when I end the contract and onboarding a replacement.

I usually keep the job post open until the person has satisfactorily completed their first task and we’re happy with the time/process. That way, if I need to hire someone else, I can choose from the pool of applicants that I’ve already shortlisted. Depending on whether I have tasks that can be broken down and done in parallel (ex: data entry), I might hire several people with the understanding that I’ll choose one or two going forward.

Coordinating

I send most tasks by e-mail because that’s the most convenient for me. I use Skype or Google Hangout to explain tasks in more detail. Since Skype tends to perform badly when I’m out and about, I also give assistants my cellphone number. I’ve been trying to get people set up using my VOIP phone so that they can call me, but we haven’t sorted that out yet. The easiest way might be for me to fund a company Skype account and have them call me with that.

I don’t want to require people to shift their timezone / sleeping habits – some of my friends have done overnight shiftwork before, and it really messes up one’s social life. Since my virtual assistants have access to my calendar, they can either use that to directly book me or use ScheduleOnce to find a time that works with their schedule.

I try to remember to specify due date and time budget (ex: spend a maximum of 2 hours on this, then send me whatever you have so that we can make sure you’re on the right track). The due date typically works, although I don’t think anyone’s been paying attention to the time specifications yet. I might revisit the Four Hour Work-week’s templates for getting these things communicated.

I hate the idea of tasks falling through the cracks especially if assistants get preoccupied with other things, so I’ve been experimenting with project-management applications like Trello or Asana. I want to be able to see what tasks I’ve assigned to people, what’s waiting for a response, and what’s done. One of my assistants just updated her Trello board – hooray! I gave her a bonus to recognize her initiative. =) We’ll give that maybe six months of trying before I even think of introducing a different tool. We’ll see how this goes!

Rewards and recognition

In addition to the automatic billing that oDesk takes care of, I like catching people doing something good and giving them an unexpected bonus. I always explain why I give the bonus. For example, I’m impressed when people take the initiative and when they submit excellent and timely work, especially if this is my first time working with them.

People don’t often negotiate with me for a raise, probably because my contracts tend to be shorter-term. As a client, though, I like being different by proactively giving people raises – I occasionally check my contractors’ profiles to see if they’ve raised their rates, and I’ll raise them during our existing contract because it’s good to reward good people.

I also take notes on people’s career goals and personal interests, and I try to tailor the tasks to fit them.

Dealing with miscommunication and disputes

As the employer, the buck stops with me. If someone didn’t complete something to my satisfaction, it might be because I didn’t sufficiently communicate the requirements, didn’t invest enough time in oversight or training, didn’t filter enough for skills/fit, and so on. Each mistake is a learning opportunity.

Typical mistakes and how I’m learning to deal with them:

I didn’t specify the level of detail I wanted, so I get back a War and Peace epic equivalent when I wanted Hemingway-short summaries.

Share the big picture (Why do I want this? What will I use it for?).

Provide sample output.

Give a time budget, so that people get back to me after 2-4 hours instead of spending two days on a task. (Still working on getting people to follow this…)

People promise to work on something, but end up not doing it. It happens; people can be over-optimistic about their time.

Set earlier deadlines than I need, and give myself leeway to try someone else or do it myself.

Follow up. Then follow up again. If necessary, take the task back.

I get the output back and think I should probably have done it myself instead (skills, background knowledge, whatever).

Breathe.

See the value in a first draft and alternative perspectives. Focus on the good.

Remember the additional benefits of this delegation experiment – it’s not just about saving time, it’s also about learning how to give instructions and work with other people.

I find that some steps are missing.

Consider whether the steps are truly necessary.

Review the process and flesh out the steps. Explain why the steps matter.

Turn the process into a checklist. Add the checklist to my e-mail templates if needed.

Keep a closer eye on tasks, at least until the process is sorted out

An assistant is uncommunicative / unreachable.

I take back any tasks needed.

I follow up to see what’s going on. Life happens, and people sometimes need support and understanding to get through rough spots.

If they’ve become too busy to work on my tasks or they’ve gone AWOL, I shrug that off as a cost of doing business, and pick up the threads from there.

For chronic mistakes: If I get along with the person, I might give them different kinds of tasks instead. I might end the contract, but be open to hiring them again in the future. If I feel really uncomfortable, I end the contract and resolve not to hire them again, which has happened in a couple of cases. That’s also a good prompt to go back and think about how I can improve my hiring and training processes.

Ways to improve

I sometimes get distracted by other things I’m working on, so I end up not sitting down and investing in delegating tasks. I’ve attempted to address that by giving people 10-25% discretionary time for learning things and brainstorming other ways they can help me, but assistants seem to be reluctant to take this self-directed time, so I may need to tweak how I communicate it. Maybe I should turn it into a formal task, or establish a weekly wask – “I want to give you at least 5 hours of work each week, and if I don’t, please use one hour to brainstorm ways you can help me and send me a note.” Hmm…

Another tip from one of my role models was to involve assistants in your weekly review so that they can help you with your big picture. One of my assistants has a long-term career interest in HR, so I’ve just invited her to set up a weekly one-hour meeting with me where we can review what I’m working on and what I’m planning to do next. Maybe she can help me brainstorm what and how to delegate. I think that would be great, and possibly more useful than the discretionary time idea (at least for starters, until people get a better sense of the big picture and trust that I won’t blow up at them for learning something.)

What else would you like to know about how I delegate? Do you have any tips that can help me do this better?

Most companies try to be hush-hush about good people. That makes sense. You don’t want to train people and then have them headhunted away from you. Hiring can be expensive and distracting.

I want to see what happens if you turn that upside down. Other people have been asking me about my delegation experiments in scheduling, data entry, and other areas. I’m really happy with the virtual assistants I have. I wanted to them to find as much work as they want doing the kind of work they want. I’m happy to recommend the people that I like to the people that I like.

Will this come back to bite me? Maybe. My assistants’ workloads may get to the point where they don’t have time to work on my tasks because the tasks they do for other people are so much more interesting. My first reaction is to think of this as a bad thing, but when you dig deeper, it’s not actually that scary.

I’m reminded of something that I read in the E-Myth Enterprise:

People-oriented companies depend on "good" people to produce results, where "good" is defined as experienced, successful, self-motivated—in short, people who can be depended upon to produce good results. Someone is always shouting, "Find me someone who knows how to get the job done!" in a people-oriented company.

Process-oriented companies depend on good processes to produce results, where good is defined as the process’s ability to produce the very best results in the hands of inexperienced (or less experienced) people than the competition needs to produce the same results.

I don’t want to rely on just working with good people. I want to build up good processes that can harness good people. If I get to the point where I need to hire someone else because my assistants have become integral to someone else’s business or life, that’s not so bad. I’ll get more experience in hiring. Each person gives me another opportunity to improve my processes and learn from somebody new. I actually enjoy the hiring process, although it also makes me feel mixed emotions – such a candy store of talent out there! I don’t mind doing more of it.

It’s not like the churn that happens when you burn people out and discard them. I want to get to the point where working with me is an excellent launch pad, and where I have great onboarding and offboarding processes to make it even easier.

If any of my delegation experiments sound interesting and you think you might want to invest in trying that out too, talk to me. Share what you’re learning and what you hope to learn. If you sound like an okay sort of person – I don’t want to waste my assistants’ time in interviews or have them burned by someone who doesn’t work out – I’ll introduce you to the appropriate assistant, and both of you can see if it’s a good fit. =)

I think we’ve got this scheduling process sorted out, and I really really like it. It turns out that I didn’t have to fuss about with lots of templates or worry so much about exceptions.

When I’m reaching out by e-mail, all I have to do is cc: my assistant and add a short paragraph with details. She knows how to handle things. She knows my preferences for in-person and online meetings. She can follow up and make things happen.

So far, amazing. Things appear on my calendar! I can send Criselda a long e-mail with the AngelHack schedule for the weekend, ask her to pull out just the 2:15pm demo and block off 1h before / 2h after for travel, and it appears on my calendar with the venue information and other things I need to know. I feel comfortable asking her to coordinate with multiple people. This is good.

Here are a few things we’ve done to make it nice and smooth:

I used Google Calendar to share my calendar with her so that she has full edit access to it without being able to access the rest of my e-mail. Stephan Spencer has his assistants process his e-mail for him – I’ll get to that level of trust someday!

I set up an account for her on Google Apps. Because she uses a @sachachua.com address, I feel like I need to explain less about who she is, and I worry less about offboarding.

I add the person’s name to the subject line: That way, when she’s reviewing her inbox, she can easily distinguish the different conversations.

We use Trello to keep track of task status: I want to be able to see whom we’re waiting for a response from and the status of other tasks I’ve assigned her, and Trello makes it easy to do that. I do most of the Trello task updates, but I hope we’ll get the hang of updating the boards together.

Who’s interested in talking about delegation and scheduling? We can look into scheduling a Google Hangout!

Scheduling stresses me out. I’ve had several calendar hiccups before: wrong dates, ambiguous locations, no contact information (or incorrect ones!), and so on. I want to fix that so that I can get better at meeting people and following up.

What would success look like? I think it would be awesome to get to the point where I can easily set lunches, coffees, and calls with people. This is how that process might look like:

I bump into people in person or get an email from them. If I meet them in person, I scan in or take a picture of their business card and add it to my file.

I introduce my assistant through e-mail and ask him/her to schedule lunch/coffee/a call. I use an e-mail template on my computer or a snippet on my phone to make sure that I include all the information necessary. My assistant also refers to a note with my preferences and processes.

My assistant contacts the person and negotiates schedule / location using http://scheduleonce.com or manual scheduling through e-mail, following up in case people don’t respond. If possible, we’ll suggest a venue with good WiFi near the person’s office or location. He or she would create a calendar entry for the meeting as well as travel/preparation time around it.

We have a task board where I could see where people are in the process, so I can be sure that nothing slips through the cracks. My assistant updates it, and we review it periodically.

It’s important to me that the process doesn’t make people feel like I’m standoffish or self-important. I also want to make sure that we don’t drop the ball even if I change assistants or take tasks back, so I want to use something like Trello to track scheduling status.

Here are some templates that I’m thinking of using:

Sample e-mail introducing the assistant and asking her to set things up

Hello, John!

I’d love to meet with you for lunch to discuss sketchnoting – my treat. Criselda (cc’d here) will be helping us set up something that works with your schedule. Criselda: Could you please organize lunch for maybe the second week of December? Thank you!

Sacha Chua

Sample e-mail from assistant

Hello, John!

I’m Criselda, and I’m looking forward to helping you and Sacha get together for a great conversation about sketchnotes. For lunch, would either Dec 10 (Mon), Dec 11 (Tue), or Dec 13 (Thu) work for you? 12pm usually works, but she’s happy to meet earlier or later if needed. Alternatively, if none of those dates work for you, you can check her availability at http://meetme.so/sachac or send me a few dates and times that fit your schedule.

Also, where will you be at that time? If you’ll be near your office at 123 Anywhere Street, I can find a restaurant nearby. If you’ll be elsewhere, tell me and I’ll look for somewhere close – anywhere near the subway line would be fantastic. Got a favourite? We’d love to find out about it!

What phone number would be the best to reach you at in case something comes up?

This is Criselda again. I’ve set up the calendar invitation for your meeting with Sacha for 12pm on Dec 13 at Restaurant Name. Please tell me if you’re having problems adding it to your calendar. If you need to reschedule, please feel free to get in touch with me. You can check http://meetme.so/sachac for Sacha’s updated availability. If you’re rescheduling on the same day, please call Sacha at 416-823-2669. Thank you, and I hope you have a great conversation!

Criselda Hernandez

What do you think? If I used a process like this to schedule something with you, would you feel weird about it? What would make it better? Have you delegated or are you in the process of figuring out how to delegate! I’d love to talk to you!

One of my business validation experiments has suddenly kicked into high gear. People love the sketchnotes I’ve been taking. Since they’re interested in illustration and event coverage, I’m happy to take advantage of that opportunity to learn more about business. I want to see where we can take this. In addition, I want to connect with way more people and find out how I can help them.

I’ve been investing more time into delegation as a way to buy time and share opportunities. One of the small processes I’d like to delegate is scheduling, which can be quite stressful for me. I often review my mail on the subway, and it’s difficult for me to look up locations or refer to notes. I worry about time zones and missed connections, so I want to make sure that there are calendar entries at the right time, with the right people, and with backup contact information. As I dig deeper into validating business ideas and connecting with people, I’ll be trying to set up appointments with so many people that I’d worry about dropping the ball, not getting back to people, or not following up in case people haven’t gotten back to me.

Software tools such as ScheduleOnce aren’t quite there yet in terms of completely handling the scheduling process. I want to be able to delegate appointment-setting to someone who can arrange times, suggest venues, make sure important information is included in the event description, and follow up as needed.

One of my friends was open to the idea of working as my virtual assistant, so I set her up on oDesk and gave her access to my accounts. It’s good to know people you can trust with your Google account. While you can delegate without giving full mail and calendar access, some things are just easier when people can find what they need. I did set up a separate email account for her so that she wouldn’t have to clutter her personal mail with all the requests.

Even though we’re just starting out, it’s such a relief to be able to forward her mail and know that she’s going to keep track of things. We’re not quite at a smoothly running process yet, but maybe we’ll get there in the next few weeks. I’d love to get to the point where I have a few keyboard shortcuts for templates that explain what’s going to happen (including details she’ll need in order to plan), and she’ll follow up and make it happen. I’d also like to be able to keep track of the people that we’re trying to reach and where we are in the process. She’s been busy catching up with other work this week, but I hope that as her coursework settles down and we work out the kinks in the process, things will run even more smoothly.

I’m also experimenting with automated ways to make it easier to arrange times. ScheduleOnce seems to be the most promising of the bunch. Doodle often gets timezones quietly wrong, and Tungle is just about to close its doors. I’m not completely sold on ScheduleOnce, but people seem to have the fewest problems scheduling with it. There’s so much more to setting appointments, though.

If we’ve got a lunch, coffee, or call coming up in the next month or so, I appreciate your patience as we experiment with the scheduling process!

I’m curious about this because I’ll need it in order to scale, and because it’s one of those universal things. How do people learn how to manage? How can I learn? I’ve read tons of books and blog posts. I’ve heard lots of advice and stories. We have a sense of what good management looks and feels like, and we’re all too familiar with examples of bad management. How do you bridge the gap from theory to practice?

How do you grow into becoming a good manager or a great one? Do we leave it to people who figured out the rules in grade school – “natural leaders”? We don’t get lots of practice or lessons in managing, probably because it’s so easy to step back and let other people make decisions. But the lack of management skills can get in the way of making good things happen, so it’s good to learn how to manage.

What does it look like to consciously develop this skill of orchestrating people’s work and energy? How can you gradually learn it in low-risk situations instead of waiting for workloads to force your hand?

I want to learn more about how to align people and help them grow while creating more value than one could create alone. The world is this candy store of people with awesome skills and possibilities. There’s just so much out there that I’d like to be able to draw on.

On one of my consulting engagements, we have a high school intern who’s doing wonderfully. I’m delighted to have the opportunity to help pick some of his tasks and delegate some things I’ve been working on. I learn from the way he does things, and I enjoy looking for ways for him to make the most of his internship. I haven’t been paying much attention to my outsourcing experiments over the last few months, but I bet that I could learn a lot if I paid close attention to it, going beyond transactions to help people grow. I’ve done that in the past with other assistants, and I really liked the results.

Here’s what wild success might look like: I find good people and help them grow their skills, either working on things I’d like to see happen or good things that people are willing to pay for. Success would be a great fit between the person and the work that needs to be done. They might grow enough to be able to handle these things on their own, in which case I can grow a network of freelancers, or they might prefer the benefits of working with a team. I find clients who have flexible timelines (so that I have time to coach or even do the work if necessary) and are okay with me delegating the work so that people grow, or I find a project I believe in strongly enough to fund and bootstrap until it’s been fleshed out enough to be worth investing in.

Step 1 might be to map people’s interests, skills, and growth plans. Step 2 is trickier. How can I put on training wheels so that I can try things with friendly clients on non-risky projects without taking on too much risk myself? I’m scaling down my consulting work, but I can postpone part of my next experiment if contracting is a better way to learn this. What if I focus on, say, Rails or WordPress stuff, with the understanding that I’ll pair-program with someone, maybe like the apprenticeship systems of the past? I’m fine with Rails, Drupal, and WordPress development, but new to independent contracting, so maybe I should approach it as a learner first – partnering up with someone for a few projects?

What about non-web development ways to learn this? I can delegate more of my processes, and see if other people would be interested in delegating or expanding theirs. That’s something I’m curious about, actually. People need help learning how to give good instructions and build working relationships. It’ll be interesting to see if I can do that in a way that adds value. I think that might actually be more promising than development because I won’t be distracted by the technical side of things. I’ll need to find out if people are looking for help in getting started with delegation. In terms of alternate business models, it might be an agency structure, process libraries, and e-books. Hmm… That would look like phone or Skype conversations about what people want to do, then coordinating with service providers. There are quite a few companies that do this already, but process libraries, automation, and growth might make a difference.

Recent comments

JohnKitchin Thanks. That matches my current understanding too. It seems like use-package pretty conveniently installs and configures packages. I have seen cask for creating and installing... – Emacs configuration and use-package